Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-glucitol)

被引：44

作者：

Joseph, CC ^{[1
]}

Regeling, H ^{[1
]}

Zwanenburg, B ^{[1
]}

Chittenden, GJF ^{[1
]}

机构：

[1] Univ Nijmegen, NSR Ctr, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

来源：

TETRAHEDRON | 2002年 / 58卷 / 34期

关键词：

azasugars; iminosugars; glycosidase inhibitors; D-mannoazepane; D-glucoazepane;

D O I：

10.1016/S0040-4020(02)00757-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6907 / 6911

页数：5

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